Modified silane compounds

Abstract

This invention relates to the reversible protection of hydroxy-silane functional groups by acid cleavable protecting groups. The development of reversible protecting groups greatly enhances the current utility of silanes while introducing further novel applications. For instance, reversibly protected silanes are of particular value in applications where room temperature cure and/or adhesion is of value, such as coatings, high resolution imaging, caulks, adhesives, sealents, gaskets, and silicones. Reversibly protected silanes can also be beneficially used in reticulating agents, and in sizing agents, tires, and release coatings. The incorporation of reversibly protected silanes into coating resins is of particular value. The reversibly protected silane can be incorporated into the coating resin by polymerizing a monomer containing the reversibly protected silane into the resin or by post-addition into the coating formulation. The reversibly protected silane remains protected under basic conditions, such as in a coating formulation that contains a volatile base, for instance ammonium hydroxide. However, deprotection occurs under mildly acidic conditions. Thus, as a coating formulation containing a volatile base dries the volatile base evaporates and deprotection occurs. This allows for controlled room temperature crosslinking to occur with hydroxy-functionalized polymers. The present invention more specifically discloses a silyl-acetal compound consisting of a silane having 3 or 4 acetal moieties bonded thereto.

1. An aqueous polymer composition suitable for use as an adhesive, caulk, sealant, or coating which is comprised of (I) an acid; (II) a volatile base; wherein the amount of volatile base present is sufficient for the aqueous polymer composition to have a pH greater than 7; (III) water; (IV) a resin having repeat units which are derived from (a) a a monomer selected from the group consisting of vinyl monomers, vinyl aromatic monomers, conjugated diolefin monomers, and acrylic monomers and (b) a silicon containing monomer having a structural formula selected from the group consisting of: 
       
         
           
           
               
               
           
         
       
       wherein n represents an integer from 1 to 3; wherein m represents an integer from 1 to about 20; with the proviso that m can represent the integer 0 for structures of formula (3) wherein Z represents the group C(R)R′; wherein X′ groups can be the same or different; wherein X′ represents an unsaturated moiety containing at least one non-aromatic double bond; wherein R, R′, and R″ can be the same or different and are selected from the group consisting of hydrogen atoms, alkyl groups containing from 1 to about 12 carbon atoms, aryl groups containing from about 6 to about 18 carbon atoms, alkaryl groups containing from 7 to about 18 carbon atoms, alkoxy groups containing from 1 to about 18 carbon atoms, hydroxy groups, and halide atoms, wherein R* is selected from the group consisting of hydrogen atoms, alkyl groups containing from 1 to about 12 carbon atoms, axyl groups containing from about 6 to about 18 carbon atoms, and alkaryl groups containing from 7 to about 18 carbon atoms; wherein R, R′, R″, and R* can be bonded together in any combination in cases where R. R′, R″, and R* are not hydrogen atoms, halide atoms, or hydroxy groups; wherein Y represents a moiety selected from the group consisting of C(R)R′, oxygen, sulfur, nitrogen, and phosphorus; wherein Z represents a moiety selected from the group consisting of C(R)R′, oxygen, sulfur, nitrogen, and phosphorus; with the proviso that Y and Z can not both represent the moiety C(R)R′; wherein the contiguous cyclic ring in formulas (1) and (3) can contain heteroatoms selected from the group consisting of oxygen, sulfur, nitrogen, phosphorus, and silicon in cases where m represents an integer greater than 1; wherein the contiguous cyclic ring in formulas (1) and (3) can be saturated or unsaturated in cases where m represents an integer greater than 1; wherein said alkyl groups, axyl groups, alkaryl groups, and alkoxy groups can contain halide atoms and heteroatonis selected from the group consisting of oxygen, sulfur, nitrogen, phosphorus, and silicon; (V) optionally, a wetting agent; (VI) optionally, a defoamer; and (VII) optionally, a pigment; (VIII) optionally, a filler; and (IX) optionally, an extender. 
     
     
       2. An aqueous polymer composition as specified in  claim 1  wherein the volatile base is ammonia. 
     
     
       3. An aqueous polymer composition as specified in  claim 1  wherein the volatile base is ammonium hydroxide. 
     
     
       4. An aqueous polymer composition as specified in  claim 1  wherein the silicon containing monomer is of the structural formula: 
       
         
           
           
               
               
           
         
       
     
     
       5. An aqueous polymer composition as specified in  claim 1  wherein the silicon containing monomer is of the structural formula: 
       
         
           
           
               
               
           
         
       
     
     
       6. An aqueous polymer composition as specified in  claim 1  wherein the silicon containing monomer is of the structural formula: 
       
         
           
           
               
               
           
         
       
     
     
       7. An aqueous polymer composition as specified in  claim 1  wherein the silicon containing monomer is of the structural formula: 
       
         
           
           
               
               
           
         
       
     
     
       8. An aqueous polymer composition suitable for use as an adhesive, caulk, sealant, or coating which is comprised of (I) an acid; (II) a volatile base; wherein the amount of volatile base present is sulficient for the aqueous polymer composition to have a pH greater than 7; (II) water; (IV) a resin having repeat units which are derived from (a) a monomer selected from the group consisting of vinyl monomers, vinyl aromatic monomers, conjugated diolefin monomers, and aciylic monomers and (b) a silicon containing monomer having a structural formula selected from the group consisting of: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
       wherein m represents an integer from 1 to about 20; wherein X′ groups can be the same or different; wherein X′ represents an unsaturated moiety containing at least one non-aromatic double bond; wherein Q is selected from the group consisting of hydrogen atoms and SiX′ 3 ; wherein R and R′ can be the same or different and are selected from the group consisting of hydrogen atoms, alkyl groups containing from 1 to about 12 carbon atoms, aryl groups containing from about 6 to about 18 carbon atoms, alkaryl groups containing from 7 to about 18 carbon atoms, alkoxy groups containing from 1 to about 18 carbon atoms, hydroxy groups, and halide atoms; wherein R* is selected from the group consisting of hydrogen atoms, alkyl groups containing from 1 to about 12 carbon atoms, aryl groups containing from about 6 to about 18 carbon atoms, and alkaryl groups containing from 7 to about 18 carbon atoms; wherein R, R′, and R* can be bonded together in any combination in cases where R, R′, and R* are not hydrogen atoms, halide atoms, or hydroxy groups; wherein Y represents a moiety selected from the group consisting of oxygen, sulfur, nitrogen, and phosphorus; wherein Z represents a moiety selected from the group consisting of C(R)R′, oxygen, sulfur, nitrogen, and phosphorus; wherein the contiguous cyclic ring in formulas (5), (6), (7), (8), (9), (10), (11), (12), (13), and (14) can contain heteroatoms selected from the group consisting of oxygen, sulfur, nitrogen, phosphorus, and silicon in cases where in represents an integer greater than 1; wherein the contiguous cyclic ring in formulas (5), (6), (7), (8), (9), (10), (11), (12), (13), and (14) can be saturated or unsaturated in cases where m represents an integer greater than 1; wherein said alkyl groups, aryl groups, alkaryl groups, and alkoxy groups can contain halide atoms and heteroatoms selected from the group consisting of oxygen, sulfur, nitrogen, phosphorus, and silicon; (V) optionaliy, a wetting agent; (VI) optionally, a defoamer; and (VII) optionally, a pigment; (VIII) optionally, a filler; and (IX) optionally, an extender. 
     
     
       9. An aqueous polymer composition as specified in  claim 8  wherein the volatile base is ammonia. 
     
     
       10. An aqueous polymer composition as specified in  claim 8  wherein the volatile base is ammonium hydroxide. 
     
     
       11. An aqueous polymer composition as specified in  claim 8  wherein the silicon containing monomer is of the structural formula: 
       
         
           
           
               
               
           
         
       
     
     
       12. An aqueous polymer composition as specified in  claim 8  wherein the silicon containing monomer is of the structural formula: 
       
         
           
           
               
               
           
         
       
     
     
       13. An aqueous polymer composition as specified in  claim 8  wherein the silicon containing monomer is of the structural formula: 
       
         
           
           
               
               
           
         
       
     
     
       14. An aqueous polymer composition as specified in  claim 8  wherein the silicon containing monomer is of the structural formula: 
       
         
           
           
               
               
           
         
       
     
     
       15. An aqueous polymer composition as specified in  claim 8  wherein the silicon containing monomer is of the structural formula: 
       
         
           
           
               
               
           
         
       
     
     
       16. An aqueous polymer composition as specified in  claim 8  wherein the silicon containing monomer is of the stmctural formula: 
       
         
           
           
               
               
           
         
       
     
     
       17. An aqueous polymer composition as specified in  claim 8  wherein the silicon containing monomer is of the structural formula: 
       
         
           
           
               
               
           
         
       
     
     
       18. An aqueous polymer composition as specified in  claim 8  wherein the silicon containing monomer is of the structural formula: 
       
         
           
           
               
               
           
         
       
     
     
       19. An aqueous polymer composition as specified in  claim 8  wherein the silicon containing monomer is of the structural formula: 
       
         
           
           
               
               
           
         
       
     
     
       20. An aqueous polymer composition as specified in  claim 8  wherein the silicon containing monomer is of the structural formula: